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Oregon

$140+ Cheap flights from Caribbean Islands to Oregon

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Oregon

Cheapest flights from Caribbean Islands to Oregon
Explore the most affordable flight options available from Caribbean Islands to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.

This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:10 am
SJU
-
PDX
2 stops14h 05m
Southwest
Sat 4/258:00 am
PDX
-
SJU
2 stops12h 40m
Southwest
Deal found 2/3$408
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/211:00 pm
SJU
-
PDX
1 stop12h 02m
Delta
Fri 4/2412:30 am
PDX
-
SJU
1 stop11h 42m
Delta
Deal found 2/1$440
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/242:23 pm
SJU
-
PDX
1 stop13h 27m
American Airlines
Sat 2/289:44 pm
PDX
-
SJU
1 stop12h 09m
American Airlines
Deal found 2/1$449
This Faresmojo deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2512:30 pm
SJU
-
PDX
1 stop12h 55m
JetBlue
Tue 6/3011:40 pm
PDX
-
SJU
1 stop13h 25m
JetBlue
Deal found 2/1$451
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:56 pm
SJU
-
PDX
1 stop10h 54m
United Airlines
Thu 5/1410:16 pm
PDX
-
SJU
1 stop10h 48m
United Airlines
Deal found 2/3$465
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:10 pm
SJU
-
PDX
2 stops14h 05m
Southwest
Wed 3/118:40 am
PDX
-
SJU
2 stops12h 35m
Southwest
Deal found 2/4$470
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:35 pm
SJU
-
PDX
2 stops12h 47m
American Airlines
Tue 8/2511:59 pm
PDX
-
SJU
2 stops15h 16m
American Airlines
Deal found 2/3$478
This American Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
SJU
-
PDX
1 stop20h 18m
American Airlines
Thu 5/2811:30 pm
PDX
-
SJU
1 stop20h 21m
American Airlines
Deal found 2/4$490
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1111:59 pm
SJU
-
PDX
1 stop20h 00m
American Airlines
Fri 5/1511:47 pm
PDX
-
SJU
1 stop11h 32m
American Airlines
Deal found 2/3$493
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:59 pm
SJU
-
BOI
1 stop15h 04m
American Airlines
Wed 4/156:43 am
BOI
-
SJU
1 stop14h 19m
American Airlines
Deal found 2/2$499
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:25 am
SJU
-
BOI
2 stops12h 45m
Southwest
Wed 4/156:00 am
BOI
-
SJU
2 stops13h 05m
Southwest
Deal found 2/2$501
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:40 pm
SJU
-
BOI
1 stop9h 42m
United Airlines
Wed 4/155:00 am
BOI
-
SJU
2 stops13h 38m
United Airlines
Deal found 2/2$510

Find flight deals from Caribbean Islands to Oregon

Keep the following information in mind while searching for Caribbean Islands to Oregon flight deals. Data was last updated February 5, 2026.

Round-trip from

$408
(Southwest)

One-way from

$140
(Kiwi.com)
From Caribbean Islands to Oregon
Search Deals
One-way flight from Caribbean Islands to Oregon
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Oregon that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 5, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Oregon that are best for you.

Fly from

Caribbean Islands

Fly to

Oregon

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 4/21

8:10 am-7:15 pm

2 stops14h 05m

Portland

Sat 4/25

8:00 am-11:40 pm

2 stops12h 40m

$408

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 4/21

7:25 am-8:19 pm

1 stop15h 54m

Portland

Sat 4/25

1:52 pm-4:32 am

1 stop11h 40m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 5/11

3:56 pm-11:50 pm

1 stop10h 54m

Portland

Fri 5/15

10:55 pm-2:44 pm

1 stop12h 49m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/30

1:31 pm-11:53 pm

2 stops13h 22m

Portland

Tue 5/5

11:47 pm-2:52 pm

2 stops12h 05m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/2

6:00 am-12:22 am

1 stop21h 22m

Portland

Sat 4/11

6:00 am-4:32 am

1 stop19h 32m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 4/3

7:11 am-12:22 am

1 stop20h 11m

Portland

Mon 4/6

9:44 pm-8:51 pm

1 stop20h 07m

$440

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 4/8

11:59 pm-1:03 pm

1 stop15h 04m

Boise Air Term. Gowen Fld

Wed 4/15

6:43 am-11:02 pm

1 stop14h 19m

$499

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 4/8

11:25 am-10:10 pm

2 stops12h 45m

Boise Air Term. Gowen Fld

Wed 4/15

6:00 am-9:05 pm

2 stops13h 05m

$501

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 4/8

1:40 pm-9:22 pm

1 stop9h 42m

Boise Air Term. Gowen Fld

Wed 4/15

5:00 am-8:38 pm

2 stops13h 38m

$510

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Tue 3/3

7:00 am-10:22 pm

2 stops18h 22m

Boise Air Term. Gowen Fld

Mon 3/9

6:33 pm-9:00 am

2 stops12h 27m

$519

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 52 results
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Best time to book a flight from Caribbean Islands to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Caribbean Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Oregon

What is the cheapest month to book a flight from Caribbean Islands to Oregon?

Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Oregon (average of $228). Flying from Caribbean Islands to Oregon in October is currently the most expensive (average of $481). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oregon. Reviews last updated February 5, 2026.
Read reviews from past customers who have flown American Airlines from Caribbean Islands to Oregon. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,222 reviews

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,222 reviews
American Airlines
7.2
Good
11,222 reviews

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Caribbean Islands to Oregon?

    Airlines like Southwest, American Airlines, and United Airlines fly from Caribbean Islands to Oregon in about 9h 42m. The time it takes to get you to your destination can typically vary by up to 6h 12m. There are 3374 mi between Caribbean Islands and Oregon. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean Islands to Oregon one-way?

    The cheapest airlines for a one-way flight from Caribbean Islands to Oregon are JetBlue ($180), United Airlines ($184), and Delta ($184).

  • Can I find deals for flights from Caribbean Islands to Oregon that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands to Oregon?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Oregon.

  • Can I find deals for business class flights from Caribbean Islands to Oregon?

    Yes. Cheapflights offers flight deals from Caribbean Islands to Oregon by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Caribbean Islands to Oregon?

    Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Oregon (average of $228). Flying from Caribbean Islands to Oregon in October is currently the most expensive (average of $481). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Caribbean Islands to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Caribbean Islands to Oregon

Discover the top 4 airlines that operate flights from Caribbean Islands to Oregon. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$379Average$550FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$575FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

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